#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006367.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2006367
loop_
_publ_author_name
'Kubo, Kanji'
'Kato, Nobuo'
'Mori*, Akira'
'Takeshita*, Hitoshi'
_publ_section_title
;
1-(8,8-Dicyanoheptafulven-3-yl)aza-15-crown-5 Ether
;
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1136
_journal_page_last               1137
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C20 H25 N3 O4'
_chemical_formula_sum            'C20 H25 N3 O4'
_chemical_formula_weight         371.43
_chemical_melting_point          134.8(8)
_chemical_name_common
;
 1-(8,8-Dicyanoheptafulven-3-yl)aza-15-crown-5 Ether
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3300(10)
_cell_length_b                   16.390(3)
_cell_length_c                   8.4840(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1976.0(5)
_diffrn_ambient_temperature      296(2)
_exptl_crystal_density_diffrn    1.249
_refine_ls_R_factor_obs          .0504
_refine_ls_wR_factor_obs         .1354
_[local]_cod_cif_authors_sg_H-M  'P 21/a'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '134--135.5' was changed to
'134.8(8)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               2006367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 .0670(9) .0879(10) .0502(8) .0023(8) .0118(7) .0162(7)
O2 .0950(14) .140(2) .0721(11) .0125(13) .0119(10) .0170(11)
O3 .066(2) .083(2) .064(2) .012(2) .0036(14) .0210(15)
O3' .072(4) .064(4) .063(3) .000(3) -.003(2) -.011(2)
O4 .0918(11) .0777(10) .0754(10) .0257(8) .0450(9) .0229(8)
N1 .0765(14) .149(2) .104(2) -.0279(15) .0122(13) -.062(2)
N2 .0704(13) .160(2) .084(2) -.0101(14) .0272(12) -.043(2)
N3 .0473(8) .0550(9) .0464(8) -.0013(7) .0077(6) .0015(7)
C1 .0476(10) .0727(12) .0467(10) .0087(9) .0081(8) -.0120(9)
C2 .0504(10) .0679(12) .0428(10) .0051(9) .0043(8) -.0110(8)
C3 .0471(10) .0553(10) .0415(9) .0049(8) .0053(7) .0030(7)
C4 .0509(11) .098(2) .0442(10) .0049(11) .0118(8) -.0100(10)
C5 .0603(12) .115(2) .0419(11) .0042(12) .0096(9) -.0195(11)
C6 .0552(11) .0854(14) .0447(10) .0010(10) .0028(8) -.0162(10)
C7 .0490(10) .0580(11) .0458(10) .0074(8) .0026(8) -.0046(8)
C8 .0506(10) .0725(13) .0527(11) .0019(9) .0069(8) -.0127(9)
C9 .0556(12) .092(2) .0707(14) -.0066(12) .0141(10) -.0224(13)
C10 .0489(11) .096(2) .0674(14) -.0042(11) .0103(10) -.0199(12)
C11 .0504(10) .0659(12) .0575(12) -.0077(9) .0026(9) -.0126(9)
C12 .0526(11) .092(2) .0450(10) -.0053(11) .0051(8) -.0067(10)
C13 .0734(15) .109(2) .0604(13) -.0145(14) .0034(11) .0309(13)
C14 .118(2) .089(2) .078(2) -.005(2) -.004(2) .0295(14)
C15 .150(3) .157(3) .104(3) .070(3) .033(2) .059(2)
C16 .083(3) .085(4) .077(3) .031(3) .000(3) .014(3)
C16' .097(9) .071(6) .100(10) -.004(7) .009(8) -.021(6)
C17 .077(2) .097(2) .074(2) .0227(13) .0232(12) .0027(13)
C18 .087(2) .080(2) .0649(14) .0237(13) .0213(12) .0016(11)
C19 .0556(11) .0651(12) .0558(11) .0063(9) .0155(9) .0120(9)
C20 .0479(10) .0591(11) .0597(11) -.0021(8) .0124(8) .0085(9)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 .90650(10) .40024(10) 1.0473(2) .0680(4) Uani d . 1 . O
O2 1.05565(15) .28743(15) 1.1309(2) .1024(7) Uani d . 1 . O
O3 1.1023(2) .2684(2) .8162(4) .0713(12) Uani d P .676(7) 1 O
O3' 1.1494(4) .3156(4) .8572(6) .068(2) Uani d P .324(7) 2 O
O4 1.02888(12) .40077(10) .5935(2) .0787(5) Uani d . 1 . O
N1 .3278(2) .3125(2) .4103(3) .1097(9) Uani d . 1 . N
N2 .3539(2) .4351(2) .8695(3) .1034(9) Uani d . 1 . N
N3 .83191(10) .48936(9) .7695(2) .0494(4) Uani d . 1 . N
C1 .57528(13) .45953(13) .7415(2) .0555(5) Uani d . 1 . C
H1 .53734(13) .47877(13) .8144(2) .067 Uiso calc R 1 . H
C2 .66581(13) .48137(12) .7754(2) .0539(5) Uani d . 1 . C
H2 .67856(13) .51221(12) .8677(2) .065 Uiso calc R 1 . H
C3 .74676(12) .46612(11) .6962(2) .0480(4) Uani d . 1 . C
C4 .73839(14) .4310(2) .5445(2) .0638(6) Uani d . 1 . C
H4 .79359(14) .4280(2) .4979(2) .077 Uiso calc R 1 . H
C5 .6590(2) .4003(2) .4554(2) .0722(7) Uani d . 1 . C
H5 .6702(2) .3827(2) .3553(2) .087 Uiso calc R 1 . H
C6 .56708(14) .38987(14) .4808(2) .0621(5) Uani d . 1 . C
H6 .52780(14) .36482(14) .3992(2) .074 Uiso calc R 1 . H
C7 .52507(13) .41243(12) .6152(2) .0512(5) Uani d . 1 . C
C8 .43043(14) .39295(13) .6261(2) .0586(5) Uani d . 1 . C
C9 .3739(2) .3489(2) .5064(3) .0723(6) Uani d . 1 . C
C10 .38733(15) .4157(2) .7601(3) .0707(6) Uani d . 1 . C
C11 .84562(14) .52325(13) .9323(2) .0583(5) Uani d . 1 . C
H11A .79864(14) .56514(13) .9403(2) .070 Uiso calc R 1 . H
H11B .90698(14) .54907(13) .9505(2) .070 Uiso calc R 1 . H
C12 .83903(14) .46109(15) 1.0601(2) .0634(6) Uani d . 1 . C
H12A .85044(14) .48680(15) 1.1638(2) .076 Uiso calc R 1 . H
H12B .77656(14) .43726(15) 1.0482(2) .076 Uiso calc R 1 . H
C13 .9027(2) .3351(2) 1.1559(3) .0812(7) Uani d . 1 . C
H13A .8381(2) .3177(2) 1.1569(3) .097 Uiso calc R 1 . H
H13B .9276(2) .3524(2) 1.2623(3) .097 Uiso calc R 1 . H
C14 .9604(2) .2660(2) 1.1042(3) .0962(9) Uani d . 1 . C
H14A .9497(2) .2171(2) 1.1638(3) .115 Uiso calc R 1 . H
H14B .9422(2) .2548(2) .9922(3) .115 Uiso calc R 1 . H
C15 1.1173(3) .2279(3) 1.0807(4) .135(2) Uani d . 1 . C
H15A 1.0810(3) .1791(3) 1.0511(4) .163 Uiso calc PR .676(7) 1 H
H15B 1.1633(3) .2140(3) 1.1709(4) .163 Uiso calc PR .676(7) 1 H
H15C 1.0960(3) .1738(3) 1.1056(4) .163 Uiso calc PR .324(7) 2 H
H15D 1.1802(3) .2357(3) 1.1363(4) .163 Uiso calc PR .324(7) 2 H
C16 1.1680(4) .2500(4) .9485(7) .082(2) Uani d P .676(7) 1 C
H16A 1.2078(4) .2970(4) .9770(7) .099 Uiso calc PR .676(7) 1 H
H16B 1.2076(4) .2051(4) .9237(7) .099 Uiso calc PR .676(7) 1 H
C16' 1.1192(11) .2352(8) .9111(18) .090(3) Uani d P .324(7) 2 C
H16C 1.0566(11) .2237(8) .8574(18) .108 Uiso calc PR .324(7) 2 H
H16D 1.1612(11) .1938(8) .8785(18) .108 Uiso calc PR .324(7) 2 H
C17 1.1508(2) .3042(2) .6919(3) .0813(7) Uani d . 1 . C
H17A 1.1933(2) .2653(2) .6527(3) .098 Uiso calc PR .676(7) 1 H
H17B 1.1860(2) .3524(2) .7302(3) .098 Uiso calc PR .676(7) 1 H
H17C 1.1636(2) .2468(2) .6777(3) .098 Uiso calc PR .324(7) 2 H
H17D 1.2055(2) .3336(2) .6655(3) .098 Uiso calc PR .324(7) 2 H
C18 1.0729(2) .3255(2) .5678(3) .0764(7) Uani d . 1 . C
H18A 1.0970(2) .3276(2) .4661(3) .092 Uiso calc R 1 . H
H18B 1.0261(2) .2825(2) .5618(3) .092 Uiso calc R 1 . H
C19 .95927(14) .39802(12) .6956(2) .0581(5) Uani d . 1 . C
H19A .98674(14) .38453(12) .8029(2) .070 Uiso calc R 1 . H
H19B .91196(14) .35747(12) .6597(2) .070 Uiso calc R 1 . H
C20 .91628(13) .48248(12) .6901(2) .0551(5) Uani d . 1 . C
H20A .96306(13) .52060(12) .7391(2) .066 Uiso calc R 1 . H
H20B .90048(13) .49844(12) .5798(2) .066 Uiso calc R 1 . H
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . 1.403(3) ?
O1 C13 . 1.416(3) ?
O2 C14 . 1.400(4) ?
O2 C15 . 1.418(4) ?
O3 C16 . 1.402(7) ?
O3 C17 . 1.459(4) ?
O3' C17 . 1.418(5) ?
O3' C16' . 1.48(2) ?
O4 C19 . 1.403(2) ?
O4 C18 . 1.416(3) ?
N1 C9 . 1.149(3) yes
N2 C10 . 1.143(3) yes
N3 C3 . 1.351(2) yes
N3 C20 . 1.462(2) ?
N3 C11 . 1.478(2) ?
C1 C2 . 1.341(3) yes
C1 C7 . 1.436(3) yes
C2 C3 . 1.435(3) yes
C3 C4 . 1.401(3) yes
C4 C5 . 1.378(3) yes
C5 C6 . 1.372(3) yes
C6 C7 . 1.406(3) yes
C7 C8 . 1.408(3) yes
C8 C10 . 1.412(3) yes
C8 C9 . 1.413(3) yes
C11 C12 . 1.500(3) ?
C13 C14 . 1.500(4) ?
C15 C16' . 1.45(2) ?
C15 C16 . 1.458(7) ?
C17 C18 . 1.474(4) ?
C19 C20 . 1.513(3) ?